Thionyl Chloride → HCID 67047920, 화합물

HRID 606813노트

반응식

HRID 606813 반응식
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:15]=[N:16][CH:17]=[C:18]([CH:21]=2)[C:19]#[N:20])=[CH:8][C:7]=1[CH2:22]O>C(OCC)(=O)C>[Cl:3][CH2:22][C:7]1[CH:8]=[C:9]([C:12]#[C:13][C:14]2[CH:15]=[N:16][CH:17]=[C:18]([CH:21]=2)[C:19]#[N:20])[CH:10]=[CH:11][C:6]=1[F:5]

참가 물질

4

반응물 2

HCID 24386Thionyl Chloride2회HCID 67047751HCID 67047751, 화합물

생성물 1

HCID 67047920HCID 67047920, 화합물

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Add thionyl chloride (0.59 mL, 8.07 mmol) to a solution of 5-(4-fluoro-3-hydroxymethyl-phenylethynyl)-nicotinonitrile (1.85 g, 7.33 mmol), (prepared as described in EXAMPLE 142). After 3 h add an additional 0.2 mL of thionyl chloride and stir for another 1 h. Dilute the reaction mixture with ethyl acetate and wash with an aqueous saturated solution of sodium bicarbonate and an aqueous saturated solution of sodium chloride. Dry (sodium sulfate), filter, and concentrate. Purify the crude material by silica gel chromatography, eluting with a gradient from 85:15 to 75:25 hexanes:ethyl acetate, then elute with 50:50 hexanes:ethyl acetate to give the title compound. Further purify by additional silica gel chromatography, eluting with 90:10 (70:30 hexanes:dichloromethane):ethyl acetate. Combine clean fractions from both chromatographies and concentrate to give the title compound as a crystalline solid (1.5 g, 75%).

후처리

  1. washwash with an aqueous saturated solution of sodium bicarbonate
  2. dry with materialDry (sodium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the crude material by silica gel chromatography
  6. washeluting with a gradient from 85:15 to 75:25 hexanes
  7. washethyl acetate, then elute with 50:50 hexanes

출처 및 근거

ORD 기록
ord-1ff373ec5b184b639c4771deadf8d38c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915424B2

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